(Pyrimidin-5-yl)boronic acid → 6-(3-(Hydroxymethyl)azetidin-1-yl)-5-(pyrimidin-5-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide
Reaction equation
Br[C:2]1[C:3]([N:22]2[CH2:25][CH:24]([CH2:26][OH:27])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1>>[OH:27][CH2:26][CH:24]1[CH2:25][N:22]([C:3]2[C:2]([C:32]3[CH:33]=[N:28][CH:29]=[N:30][CH:31]=3)=[CH:21][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=3)=[O:8])=[CH:5][N:4]=2)[CH2:23]1Participants
3
Procedure
The title compound was prepared in an analogous fashion to that described in Example 128 using 5-bromo-6-(3-(hydroxymethyl)azetidin-1-yl)-N-(4-(trifluoromethoxy)phenyl)nicotinamide (Stage 135.1) and pyrimidin-5-ylboronic acid. HPLC (Condition 4) tR=4.6 min, UPLC-MS (Condition 3) tR=0.90 min, m/z=446.3 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 2.53-2.68 (m, 1H) 3.38-3.53 (m, 4H) 3.63-3.77 (m, 2H) 4.68 (t, J=1.00 Hz, 1H) 7.33 (d, J=8.99 Hz, 2H) 7.83 (d, J=8.99 Hz, 2H) 8.05 (d, J=1.96 Hz, 1H) 8.77 (d, J=1.00 Hz, 1H) 8.89 (s, 2H) 9.15-9.31 (m, 1H) 10.18 (s, 1H).
Sources & evidence
- ORD record
- ord-7870b5ac3406414e86bf66b0d6c46933
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278981B2
Reaction notes
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